The luxury home market seems to have been exploding not only in New York City but in Chicago as well. As listings priced as high as $32 million have been redefining the high end of the Chicago home market, at PropertyShark we compiled a list of the priciest home sales of each year since 2006 to see just how impressive the transactions were in the recent past.

The results of our analysis show that closing prices for post-Lehman real estate transactions in Chicago clearly reflect the crash in the economy (see how prices dropped in 2009 in the table at the bottom of this post), and  that most top-dollar homes are clustered in wealthy neighborhoods such as Gold Coast and Lincoln Park. Gain a better insight into what makes each property so valuable by reading below:

2006      1435 North Astor Street, Chicago

This prestigious turn-of-the-century neoclassical mansion was designed by Thomas and Rapp in 1894 and redone by Henry Ives Cobb in 1902. In May 2006 the 13-fireplace home found an owner willing to pay $14.5 million, which placed it at the top of the Chicago residential sales market…so far, at least.

2007    1254 North Lake Shore Drive, Chicago

This 1891 stone mansion spreading over almost 9,000 square feet was bought in March 2007 for yet another super-sized price – $10,100,000.  Prior to the sale, the house was home to Chicago financier Jim Tyree and his wife Eve, who restored the then 2-unit property to its original single-family function.

2008   1425 North Astor Street, Chicago

Built in 1918 for real estate developer William D. Kerfoot, this one-of-a-kind property completes the elegant aspect of Chicago’s Astor Street. If you add to its historic value the large lot size, 7,372 square feet, and the exclusive location, you begin to understand why the owners paid $13 million for this property.

2009   2021 North Howe Street, Chicago

The fact that the top sale of 2009 was priced at only $5,600,000 could be taken as a solid proof of how hard the real estate market in Chicago was hit. The 12,000 square-foot mansion built in 2006 in Lincoln Park, another upscale residential hot spot in Chicago, was sold in August after a significant price drop of more than $2 million.

2010   1866 North Howe Street, Chicago

Howe Street in Lincoln Park might be trying to match Astor Street’s reputation, judging from its density of luxury homes. However, on Howe Street new and modern is the rule. This 8,476 square -foot residence built in 2002 was sold in August for $8,500,000. Did this higher price mark the start of the housing market recovery? We can judge from the next transaction…

2011  132 E Delaware Place #6602, Chicago

This top-floor penthouse in the Bloomingdale’s Building sold for $6,890,000 in May. The owners of this exclusive condominium can enjoy panoramic views of the lake and the city plus access to the health club, spa and other Four Seasons hotel amenities.

2012  1340 North State Parkway #2

Can a reference to Playboy boost real estate prices? The unit at 1340 North State Parkway, the original Playboy Mansion, seems to prove so, being sold in May of this year for $5.2 million. Hefner bought the property in 1959 and donated it in 1989 to The Art Institute. In 1993 the house changed hands again, being bought by a developer who converted it into seven condos.

For a full description of each transaction, check out the table below:

Year Address Sale Price Sale Date
2006 1435 N Astor Street, Gold Coast $14,500,000 May 1, 2006
2007 1254 N Lake Shore Drive, Gold Coast $10,100,000 Mar. 1, 2007
2008 1425 N Astor Street, Gold Coast $13,000,000 Jul. 1, 2008
2009 2021 N Howe Street, Lincoln Park $5,600,000 Aug. 26, 2009
2010 1866 N Howe Street, Lincoln Park $8,500,000 Aug. 13, 2010
2011 132 E Delaware Place #6602, Gold Coast $6,890,000 May 10, 2011
2012 1340 N State Parkway #2, Gold Coast $5,200,000 May 10, 2012


Roxana Baiceanu

Roxana Baiceanu

Roxana is an associate editor with Multi-Housing News and Commercial Property Executive. In the past, she also created content for PropertyShark and Point2Homes’ blog pages. She also has 5 years of experience as a marketing copywriter.